Paramount Pictures

In this comedy, a middle-aged man juggles his problems with women, literature, and a career, while a younger man chases the artifact of his dreams. Pittsburgh college professor Grady Tripp (Michael Douglas) is currently single following his divorce from his third wife; after publishing an acclaimed first novel, Grady has been working on a follow-up, but he's been sidelined by a severe case of writer's block. Grady has more than his writing career to think about; his affair with one of the (married) chancellors at the University of Pittsburgh (Frances McDormand), has resulted in her pregnancy, while Hannah (Katie Holmes), a student boarding at Grady's house, has developed a crush on him. While Grady is obsessed with his book, one of his students (Tobey Maguire) has an obsession of his own: finding a jacket once owned by Marilyn Monroe. Based on the novel by Michael Chabon, The Wonder Boys also features Robert Downey Jr., Rip Torn, and Richard Thomas.